Disease relevance of cyclopentene

• The methylketo cyclopentenyl and 1-methoxyethyl cyclopentenyl analogues of RA were at least 50-fold more active than RA in reversing MNNG-induced hyperplasia [1].
• Treatment of mice bearing L1210 ascites with cyclopentenyl cytosine (1 mg/kg) produced rapid depletion of cytidine nucleotide pools in the tumor cells; these pools fell to 35% of control within 30 min [2].
• In situ cyclopentenyl cytosine infusion for the treatment of experimental brain tumors [3].
• A cyclopentenyl analog of retinoic acid was approximately 10-fold more effective than RA in producing mucous metaplasia [4].
• With the aim of preparing a light-insensitive bacteriorhodopsin-like pigment, bacterio-opsin expressed in Escherichia coli was treated in phospholipid-detergent micelles with the retinal analog II, in which the C13-C14 trans-double bond cannot isomerize due to inclusion in a cyclopentene ring [5].

High impact information on cyclopentene

• Analogues containing the fused cyclopentene ring are preferred to those containing the fused pyrrole ring based on growth inhibitory potency, effectiveness against decreased uptake mutants and apparent affinity for transport, and inhibition of DHFR [6].
• Pharmacokinetics and metabolism of cyclopentenyl cytosine in nonhuman primates [7].
• Among the analogs of retinoic acid, a cyclopentenyl analog, a trimethylmethoxyphenyl analog, 13-cis-retinoic acid, and alpha-retinoic acid compete for the binding site on the protein, with the cyclopentenyl analog having greater affinity than retinoic acid does [8].
• A single point mutation in CTP synthetase of Chlamydia trachomatis confers resistance to cyclopentenyl cytosine [9].
• Gold-Catalyzed Deoxygenated Cyclization of cis-2,4-Dien-1-als with Regioselective Addition of Two Nucleophiles. One-Pot Synthesis of Highly Functionalized Cyclopentene Framework [10].

Chemical compound and disease context of cyclopentene

• Lipid analysis of Mycobacterium vaccae, grown in the presence of chaulmoogric acid, demonstrates that this cyclopentenyl fatty acid is taken up by the organism and incorporated into cellular phospholipids and triacylglycerols [11].

Biological context of cyclopentene

• Palladium complexes of MAP and MOP are very efficient catalysts for allylic alkylation of racemic cyclopentenyl pivalate with [NaCH(CO2Me)2] in THF [12].
• 1592U89 was selected after evaluation of a wide variety of analogs containing a cyclopentene substitution for the 2'-deoxyriboside of natural deoxynucleosides, optimizing in vitro anti-HIV potency, oral bioavailability, and central nervous system (CNS) penetration [13].
• The synthesis features a key chelation-controlled 1,4-diastereoselective acylation to generate the quaternary carbon and an intramolecular acylation of allylsilane to build up the cyclopentene unit [14].
• CPE-C was eliminated by both renal excretion of intact drug and deamination to cyclopentenyl uracil in an apparent 2:1 ratio [15].
• To clarify the major structural features responsible for the induction of convulsions by carbapenem antibiotics, the structure-activity relationship on convulsant activity was investigated in N-acetyl-2-pyrroline and cyclopentene derivatives which correspond to the 5-membered ring containing the C-2 side chain of carbapenem antibiotics [16].

Anatomical context of cyclopentene

• The mechanism of action of the cyclopentenyl analogue of cytidine, cCyd, was investigated in human colon carcinoma cell line HT-29 [17].
• On the other hand, the cyclopentene structure may either attenuate or amplify the microsome mediated mutagenesis which is assumed to be produced by the vinyl ether portion of the molecule [18].

Associations of cyclopentene with other chemical compounds

• Several cyclopentene GABA analogues were synthesized as conformationally rigid analogues of the epilepsy drug vigabatrin and tested as inhibitors and substrates of gamma-aminobutyric acid aminotransferase (GABA-AT) [19].
• W(CO)5(L)-catalyzed endo-selective cyclization of allenyl silyl enol ethers: an efficient method for the cyclopentene annulation onto alpha,beta-unsaturated ketones [20].
• The effects of the cyclopentenyl (cCyd) and cyclopentyl (carbodine) analogues of cytidine on differentiation, and nucleic acid and nucleotide biosynthesis, were examined in the human promyelocytic leukemia cell line HL-60 [21].
• Indene and cyclopentene enaminonitriles were reacted with SCl2, iBu3N and NCS to give the first cyclopenta[1,2,6]thiadiazines that showed unusual characteristics, one as a NIR dye and another as a liquid crystal [22].
• In silico screening of pyrimidine-nucleoside analogs has revealed a number of potential lead compounds that, if bound to Mtb pyrR, could facilitate transcriptional attenuation, particularly cyclopentenyl nucleosides [23].

Gene context of cyclopentene

• A previously discovered DHODH inhibitor series was further improved by replacing the cyclopentene ring by aromatic heterocycles [24].
• A direct SN2 displacement on the cyclopentenyl mesylate 3 by the sodium salt of 6-chloro-3-deazapurine afforded the desired regioisomer 4 as the major product [25].
• SN2 reaction of the known cyclopentenyl units 12 and 13 with 2-haloadenines under basic conditions gave the protected carbocyclic nucleosides 14b,c and 15b,c, respectively [26].
• This cycloadduct ring opening methodology was applied to the synthesis of a unique cyclopentenyl hydroxamic acid-based inhibitor of 5-lipoxygenase [27].
• The deamination of CPE-C to cyclopentenyl uridine by cytidine deaminase was investigated with the purified enzyme from human placenta [28].

Analytical, diagnostic and therapeutic context of cyclopentene

• Measurement of cyclopentenyl cytosine 5'-triphosphate in vitro and in vivo by multidimensional high-performance liquid chromatography [29].

References